Compound monograph
Elamipretide
Elamipretide is a synthetic linear tetrapeptide with D-arginine, L-2′,6′-dimethyltyrosine, L-lysine and L-phenylalanine in that order, a free N-terminal amino group and a C-terminal primary carboxamide.
01
Identity & nomenclature
Elamipretide is a synthetic linear tetrapeptide with D-arginine, L-2′,6′-dimethyltyrosine, L-lysine and L-phenylalanine in that order, a free N-terminal amino group and a C-terminal primary carboxamide.
SS-31 is the admitted laboratory designation. Bendavia is a historical investigational designation. The parent registry identifiers do not identify the trihydrochloride salt.
Declared aliases and development codes: Bendavia, SS-31.
02
Molecular properties
| Molecular formula | C32H49N9O5 |
|---|---|
| Molecular mass | 639.802 Da |
| CAS Registry Number | 736992-21-5 |
| PubChem CID | 11764719 |
| UNII | 87GWG91S09 |
| Three-letter sequence | D-Arg–L-Dmt–L-Lys–L-Phe–NH2 |
Positions are numbered from the N-terminus. Dmt denotes 2′,6′-dimethyltyrosine; the primes identify aromatic-ring positions. NH2 denotes the C-terminal amide rather than another residue. A standard one-letter string is withheld because it cannot preserve D-Arg1 or the two ring methyl groups of Dmt2; this chemistry is outside the automated sequence-formula model.
03
Structural characteristics
The molecular formula and average mass describe the unsalted, unhydrated parent peptide. Two ring methyl substitutions contribute C2H4 relative to tyrosine. The defined structure has no disulfide.
- D-Arg at position 1
- Two aromatic-ring methyl substituents at positions 2′ and 6′ of L-tyrosine at peptide position 2
Terminal features: Free N-terminus, C-terminal amidation at Phe4.
04
Molecular targets & mechanisms
05
Analytical considerations
The CIAAW 2024 abridged calculation gives an average mass of 639.802 Da. The dossier preserves a numerical discrepancy with the GSRS value of 639.79 whose atomic-weight convention was not established. Equal formula and mass do not distinguish SS-31 from the differently ordered SS-02 peptide.
06
Verified bibliography
- Differential Effects of the Mitochondria-Active Tetrapeptide SS-31 (D-Arg-dimethylTyr-Lys-Phe-NH(2)) and Its Peptidase-Targeted Prodrugs in Experimental Acute Kidney Injury.
Wyss JC, Kumar R, Mikulic J, Schneider M, Mary JL, Aebi JD, Juillerat-Jeanneret L, Golshayan D
Frontiers in pharmacology · 2019-11-08 · Journal Article
current - Structure-activity relationships of mitochondria-targeted tetrapeptide pharmacological compounds.
Mitchell W, Tamucci JD, Ng EL, Liu S, Birk AV, Szeto HH, May ER, Alexandrescu AT, Alder NN
eLife · 2022-08-01 · Journal Article
current
10
Methodology & citation verification
Reference identity is checked against official PubMed metadata. Local deterministic receipts bind each normalized title and canonical metadata record to its verification date. Scientific values remain absent when an authoritative source has not been verified.
Read the full methodology →